Winchester MA Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,690
Status:
Active
MLS#:
73541775
Type:
Single Family
Lot size:
0.28 Acres
Year built:
1850
Courtesy: MA Properties 844-962-7767
View additional info

ADDITIONAL INFORMATION

Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,235
Status:
Active
MLS#:
73519082
Type:
Single Family
Subdivision:
Middlesex / downtown
Lot size:
0.15 Acres
Year built:
1864
Courtesy: Compass 781-219-0313
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ADDITIONAL INFORMATION

Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

Beds:
4
Baths:
5.00
Sq.Ft.:
5,233
Status:
Active
MLS#:
73518621
Type:
Single Family
Lot size:
0.25 Acres
Year built:
2004
Courtesy: Luxury Living Real Estate 617-227-7007
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ADDITIONAL INFORMATION

Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. European inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate.

Beds:
6
Baths:
5.00
Sq.Ft.:
3,403
Status:
Active
MLS#:
73510713
Type:
Single Family
Lot size:
0.24 Acres
Year built:
1966
Courtesy: Engel & Volkers Boston 617-936-4194
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ADDITIONAL INFORMATION

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.

Beds:
1
Baths:
1.00
Sq.Ft.:
613
Status:
Active
MLS#:
73500952
Type:
Condo
Year built:
1966
Courtesy: Coldwell Banker Realty - Lexington 781-862-2600
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ADDITIONAL INFORMATION

Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston

Beds:
2
Baths:
2.00
Sq.Ft.:
1,365
Status:
Active
MLS#:
73497739
Type:
Condo
Year built:
1983
Courtesy: Better Homes and Gardens Real Estate - The Shanahan Group 781-729-9030
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ADDITIONAL INFORMATION

Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail. Some photos are virtually staged.

Beds:
2
Baths:
1.00
Sq.Ft.:
810
Status:
Active
MLS#:
73496844
Type:
Condo
Year built:
1966
Courtesy: Tirana Real Estate Group 857-891-1453
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ADDITIONAL INFORMATION

BACK ON MARKET DUE TO FINANCING ! PARKVIEW WINCHESTER CONDOMINIUMS! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. Off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--2:00 PM

Beds:
5
Baths:
4.00
Sq.Ft.:
5,006
Status:
Active
MLS#:
73496396
Type:
Single Family
Subdivision:
Cox Road / High St Extension neighborhood
Lot size:
0.46 Acres
Year built:
1992
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

Beds:
6
Baths:
6.00
Sq.Ft.:
6,100
Status:
Active
MLS#:
73482275
Type:
Single Family
Subdivision:
West side
Lot size:
0.26 Acres
Year built:
2026
Courtesy: Compass 781-219-0313
View additional info

ADDITIONAL INFORMATION

Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a FIRST FLOOR bedroom suite! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston

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51–59 of 59 properties displayed
Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. Copyright © 2026 MLS Property Information Network, Inc. All rights reserved.



Winchester Real Estate

Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.

The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.

Winchester Weather

The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.

Winchester Map

Winchester Real Estate Market Conditions

  • Median sales price

    $1,825,000
    12.9%
    change since last quarter
  • # Active listings

    65
    30-day change

Winchester Schools and Demographics

Education near Winchester, MA

City County
High School Graduates 97.52 93.57
College Degree - 2 year 3.07 5.86
College Degree - 4 year 75.47 57.77
Graduate Degree 28.51 19.76
Expenditures per Student 23,560 23,560
Students per Teacher 12 12

Elementary Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Ambrose Elementary School KG - 05 458 13.5 01890
Brackett KG - 05 497 16.3 02476
Brooks School PK - 05 534 13.2 02155
Christopher Columbus PK - 05 471 11.8 02155
Clyde Reeves PK - 05 512 15.7 01801
Cyrus E Dallin KG - 05 456 15.4 02476
Daniel P Hurld KG - 05 217 14.5 01801
Goodyear Elementary School KG - 05 322 12.8 01801
Hardy KG - 05 392 16.4 02474
John A Bishop KG - 05 415 16.8 02474
John J McGlynn Elementary School PK - 05 559 13.2 02155
Lincoln Elementary School KG - 05 408 13.1 01890
Linscott-Rumford KG - 05 213 13.9 01801
Lynch Elementary School PK - 05 524 12.6 01890
Malcolm White KG - 05 336 14.7 01801
Mary D Altavesta KG - 05 235 10.8 01801
Menotomy Preschool PK - PK 57 9.5 02476
Milton Fuller Roberts PK - 05 576 13.2 02155
Muraco Elementary School KG - 05 406 12.6 01890
Shamrock PK - 05 350 13.2 01801
Thompson KG - 05 392 16 02474
Vinson-Owen Elementary School KG - 05 427 13.5 01890
Wyman KG - 05 189 13.5 01801

Middle Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Daniel L Joyce Middle School 06 - 08 528 10.6 01801
John F Kennedy Middle School 06 - 08 527 11.7 01801
John J. McGlynn Middle School 06 - 08 476 9.7 02155
Madeleine Dugger Andrews 06 - 08 494 11.5 02155
McCall Middle School 06 - 08 1,073 14.1 01890
Ottoson Middle School 06 - 08 1,107 12.7 02476

High Schools near Winchester, MA

Grades Students P/T Ratio ZIP
Arlington High School 09 - 12 1,217 13.8 02476
Curtis-Tufts 09 - 12 22 5 02155
Medford High School 09 - 12 1,176 12 02155
Winchester High School 09 - 12 1,209 14.1 01890
Woburn High 09 - 12 1,332 13.8 01801

Demographics near Winchester, MA

City County
Neighborhood Type Suburban
Population 22,875 1,623,411
Population Density 3,793 1,985
Median Age 42.4 38.5
People per Household 2.8 2.5
Median Household Income 184,844 111,790
Average Income per Capita 90,356 58,399

Real estate near Winchester